(3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone

Base Information

• Chemical Name: (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone
• CAS No.: 138125-74-3
• Molecular Formula: C₁₆H₁₃N₃O₆S
• Molecular Weight: 375.362
• Mol file: 138125-74-3.mol

Synonyms:(3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone

Chemical Property of (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone

There total 11 articles about (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

(2S,3R)-3-Hydroxy-4-(4-nitro-phenyl)-2-(2-nitro-phenylsulfanylamino)-butyric acid (137527-26-5,138125-73-2) → (3S,4R)-4-(4-Nitro-benzyl)-3-(2-nitro-phenylsulfanylamino)-oxetan-2-one (137527-28-7,138125-74-3)

Guidance literature:

With pyridine; benzenesulfonyl chloride; at 0 ℃;

DOI:10.1039/c39910001007

Reference yield: 24.0%

(2S,3R)-2-<<(2-Nitrophenyl)sulfenyl>amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid (138125-73-2) → (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone (138125-74-3)

Guidance literature:

With pyridine; 4-bromobenzenesulfonyl chloride; at -45 - 0 ℃;

DOI:10.1021/jo00027a006

Reference yield:

p-nitrophenylacetaldehyde (1460-05-5) → (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone (138125-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) lithium hexamethyldisilylamide, TiCl(NEt₂)3 / 1.) THF, -78 deg C, 30 min; hexane, -78 deg C, 1 h, 2.) THF, -100 deg C, 10 min; -78 deg C, 3.5 h

2: 85 percent / 6N aq. HCl / Heating

3: 90 percent / 1N aq. NaOH / dioxane / 0.33 h

4: 24 percent / 4-BrC₆H₄SO₂Cl, pyridine / 1.) -45 deg C, 1 h, 2.) 0 deg C, 4 h

With pyridine; hydrogenchloride; sodium hydroxide; titanium tris(diethylamido)chloride; 4-bromobenzenesulfonyl chloride; lithium hexamethyldisilazane; In 1,4-dioxane;

DOI:10.1021/jo00092a025

upstream raw materials:

(2S,3R)-3-Hydroxy-4-(4-nitro-phenyl)-2-(2-nitro-phenylsulfanylamino)-butyric acid

4-nitrobenzenesulfenyl chloride

p-nitrophenylacetaldehyde

(2R,3S)-2-Amino-3-hydroxy-4-(4-nitro-phenyl)-butyric acid ethyl ester

Downstream raw materials:

N-[(2R,3S)-2-(4-Nitro-benzyl)-4-oxo-oxetan-3-yl]-benzamide

(3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate